Fluorene Amine Epoxy Curing Agent Alkali Resistance

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Solution Overview

Problem

Aromatic amine compounds used as curing agents for epoxy compounds often result in cured products with poor alkali resistance, particularly when an aromatic amine compound with a fluorene ring linked by an amide bond is used.

Innovation Solution

An aromatic amine compound with a specific structure, where a fluorene ring is substituted by a side-chain group with two aromatic groups linked by a flexible bond, such as an amide bond, and lacks hydroxyl groups, is developed to enhance alkali resistance when reacting with epoxy compounds.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If an aromatic amine compound with a fluorene ring linked by an amide bond is used as a curing agent, then the cured product has reduced hardness and brittleness, but the alkali resistance deteriorates

Engineering Contradiction:
Improvehardness and brittlenessVSAvoidalkali resistance
Core Design Contradiction:
StrengthVSReliability

Solution Approach 1:

The invention changes the chemical structure parameters of the aromatic amine compound by introducing specific substituents (aromatic groups linked by flexible bonds at specific positions of the fluorene ring) while maintaining the core fluorene-amide structure. This structural modification allows the cured product to maintain flexibility while achieving excellent alkali resistance, resolving the contradiction between hardness/brittleness reduction and alkali resistance improvement

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining the fluorene ring system with aromatic side chains linked by flexible bonds (amide, ester, or carbamate groups). This composite structure integrates the benefits of both rigid aromatic groups (for chemical resistance) and flexible linkages (for reduced brittleness), achieving simultaneous improvement in both properties

Inventive Principle:
Principle #40Composite materials

Data Source

PatentUS11174221B2Aromatic amine compound, curing agent for epoxy compound, curable composition, cured product, method for producing cured product, and method for producing aromatic amine compound
Publication Date: 2021.11.16 TOKYO OHKA KOGYO CO LTD
  • US11174221B2 patent drawing
  • US11174221B2 patent drawing
  • US11174221B2 patent drawing

AI summary

An aromatic amine compound capable of satisfactorily forming a cured product having exceptional alkali resistance by reaction with an epoxy compound; a curing agent for an epoxy compound, the curing agent including the aromatic amine compound; a curable composition including the curing agent for an epoxy compound; a cured product of the curable composition; a method for producing the cured product; and a method for producing the abovementioned aromatic amine compound. The aromatic amine compound has a structure such that a specific position in a central skeleton comprising a fused ring such as a fluorene ring is substituted with a side-chain group including two aromatic groups linked by a flexible bond such as an amide bond, at least one amino group is bonded to the end of the side-chain group, and the structure has no hydroxyl groups.